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Chloroacetonitrile

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Chloroacetonitrile
Names
Preferred IUPAC name Chloroacetonitrile
Other names α-Chloroacetonitrile
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.153 Edit this at Wikidata
EC Number
  • 203-467-0
KEGG
PubChem CID
RTECS number
  • AL8225000
UNII
UN number 2668
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H2ClN/c3-1-2-4/h1H2Key: RENMDAKOXSCIGH-UHFFFAOYSA-N
SMILES
  • C(C#N)Cl
Properties
Chemical formula C2H2ClN
Molar mass 75.50 g·mol
Appearance colorless liquid
Density 1.193 g·cm
Boiling point 123–124 °C (253–255 °F; 396–397 K)
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H311, H331, H411
Precautionary statements P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Chloroacetonitrile is the organic compound with the formula ClCH2CN. A colorless liquid, it is derived from acetonitrile (CH3CN) by replacement of one H with Cl. In practice, it is produced by dehydration of chloroacetamide. The compound is an alkylating agent, and as such is handled cautiously.

Chloroacetonitrile is also generated in situ by the reaction of acetonitrile with sulfur monochloride. A second chlorination gives dichloroacetonitrile, which undergoes cycloaddition with sulfur monochloride to give 4,5-dichloro-1,2,3-dithiazolium chloride:

Cl2CHCN + S2Cl2 → Cl + HCl

See also

References

  1. Reisner, D. B.; Horning, E. C. (1950). "Chloroacetonitrile". Organic Syntheses. 30: 22. doi:10.15227/orgsyn.030.0022.
  2. Lebeuf, Raphaël; Berlande, Muriel; Robert, Frédéric; Landais, Yannick (2009). "Preparation of (3,5-Dimethoxy-1-Phenyl-Cyclohexa-2,5-Dienyl)-Acetonitrile Through Birch Reductive Alkylation (BRA)". Organic Syntheses. 86: 1. doi:10.15227/orgsyn.086.0001.
  3. Rees, Charles W. (1992). "Polysulfur-Nitrogen Heterocyclic Chemistry". Journal of Heterocyclic Chemistry. 29 (3): 639–651. doi:10.1002/jhet.5570290306.
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